Improvements to the Synthesis of Isofagomine, Noeuromycin, Azafagomine, and Isofagomine Lactam, and a Synthesis of Azanoeuromycin and 'Guanidine' Isofagomine

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Contents Vol 59(11)

doi:10.1071/CH06241

Improvements to the Synthesis of Isofagomine, Noeuromycin, Azafagomine, and Isofagomine Lactam, and a Synthesis of Azanoeuromycin and ‘Guanidine’ Isofagomine

Peter J. Meloncelli ^A, Robert V. Stick ^A ^B

^A Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, Crawley WA 6009, Australia.
^B Corresponding author. Email: rvs@chem.uwa.edu.au





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Australian Journal of Chemistry 59(11) 827–833 http://dx.doi.org/10.1071/CH06241
Submitted: 11 July 2006 Accepted: 25 September 2006 Published online: 17 November 2006

Abstract

Improvements in the preparation of a key imidazylate and the reduction of the derived nitrile have led to more efficient syntheses of isofagomine, noeuromycin, azafagomine, and isofagomine lactam. As well, a precursor of azafagomine has been converted into azanoeuromycin, and the nitrogen atom of isofagomine has been incorporated into a guanidine residue.